‘I paid off a poker debt with intimate favours’: Celebrities who are into gambling

Some celebrities like to spend their money on properties, luxurious cars or international trips. Others, however, like to use their fortune as a little ‘investment’ with the possibility of making more money… or losing it all. Such is the case of the following stars who have dipped their toes into the gambling world!

Back in 2020, Nelly was spotted at Mohegan Sun Casino in Connecticut. In footage obtained by TMZ, the 'Hot In Herre' rapper was reportedly involved in an alleged altercation with another poker player. In the end, a casino pit boss had to get involved, and the other gambler decided to leave despite the dealer trying to convince him to stay.

In 2006, Denise Richards testified in a sworn declation about her ex-husband Charlie Sheen's money habits. In the documents, Richards claimed the ‘Two and a Half Men’ actor used to bet on sports “every day,” losing “hundreds of thousands of dollars.” She also alleged losing money would affect in Sheen’s mood significantly.

From 2005 to 2009, ‘Spider-Man’ actor Tobey Maguire - and film producer Houston Curtis - organised game nights with other celebrities in many Los Angeles bars or hotels. Curtis himself, who met Maguire while playing poker in LA, described everything in his book ‘Billion Dollar Hollywood Heist’. He also previously admitted the stakes were so high, “winning $20,000 felt like losing".

One of Curtis and Maguire’s guests during game nights was actor Matt Damon. According to the reports, the ‘Jason Bourne’ star was not always lucky with poker and one night he even lost $50,000. Fun fact: Matt Damon starred in the 1998 film ‘Rounders’, which revolves around a former poker player who has to get in the game again, in order to help a friend pay his debts.

In 2005 Radar Online reported that the ‘Se7en’ star was part of a very interesting poker night, right after attending the Sundance Film Festival in Utah. A source close to the star told the outlet that, at some point during the game, Brad decided to make things interesting. He told the other players that “if they lost the hand they had to do some outrageous dare, but if he lost, he would pay $25,000 right there.” He ended up losing as he had the worst hand at the table, which was very suspicious. Angelina Jolie suggested at the time that her then-husband may have lost intentionally, as he kept saying “everyone deserved some help".

It seems swimming isn't Michael Phelps' only passion. The Olympic legend is no stranger to gambling and poker, and he even went onto appear at the 2018 World Series in Las Vegas. That year, he took the $3,000 Six Max place.

Former NBA superstar Antoine Walker revealed in an episode of ‘All Things Covered’, about the time he and Michael Jordan once spent 36 hours in a game of spades. He said: “Me and Michael were partners and we were playing against two other guys. They had us [behind] $900,000. I had about $100,000. "I was always a cash person. MJ had about $200,000 on him. MJ sent for half-a-million cash — sent for it.”

Actor and comedian Ray Romano created the series ‘Men of a Certain Age’, which premiered in 2009. Ray plays the main role of Joe, an aspiring golf player who never made it to the professional level. While speaking about his character to The New York Times, Romano said: “I knew I wanted Joe to have a gambling thing because I had a little gambling thing.”

In a 2017 appearance on ‘The Ellen DeGeneres Show’, Pamela Anderson talked about her exes Kid Rock and Tommy Lee… but also revealed a new partner she had met not long before the interview. The ‘Baywatch’ actress told the host that it all started during a game night. Without revealing too many details - or even a name - she said: "I was playing poker one night... and I was down about 250 grand. "He said if I made out with him, that would clear the [bet]. I paid off a poker debt with sexual favors and I fell in love. It's so romantic."

Like his pal Matt Damon, ‘Argo’ star Ben Affleck was also a frequent guest at Tobey Maguire’s game nights. However, over the past years, Ben has been spotted in different casinos with other people, or even by himself. In 2021, for instance, he was seen at Las Vegas’s Wynn Resort and Casino, specifically in the high rollers designated area.